How to address your doubts when you want to be an entrepreneur

The following is a guest post from Josh Elkin.

Your doubts are holding you back.

But you’ve dreamed of it for years:

One day you’ll leave your dead-end job in the mailroom and become your own boss.

Why your doubts are holding you back:

In your mind, your dream is perfect, but you just know that you’re not ready to make it happen yet. Something always holds you back from “one day.”

And even though you feel you’re not ready, the more you think about your dreams the more miserable you are in your current job. You’re not alone in this. Nearly 55% of Americans feel dissatisfied with their work.

There’s nothing wrong with listening to your inner voice of reason. Caution can help you fulfil your dreams. It can make you more ready and knowledgeable about the job you want to pursue.

But too much caution and listening far too often to your doubts is a dream killer. Often, we mistake doubt and fear for reason. Passionate people often experience an internal struggle, between their passions and their doubts.

They have a tendency to take for granted that their doubts are always “reasonable” and their passions are unrealistic.

My suggestion for breaking out of this cycle?

Be more logical than your doubts.

Rather than taking your doubts as truth, debate with them. Offer a strong counter-argument. Do research to find the answers to any questions you might have. Your dream is your passion, so fight for it. Don’t rush into anything recklessly, but walk forwards purposefully, and learn everything you can along the way.

So… what are some of your most common doubts?

Your doubts: common ones

Doubt #1: What if No One is Interested?

It’s hard pitching yourself to potential clients when you’re new on the scene. How can you convince them that your product or service would be valuable to them, especially when you’re not sure how valuable it actually is?

Fortunately, there are resources that can help you put yourself out there.

If you’re a freelancer, freelance marketplaces like Upwork are a great way to get started, because they’ll do the marketing for you.

If you have a product to sell, try Etsy or Amazon.

WordPress and Squarespace both offer web hosting services with plenty of website templates, so you have something to show potential customers when you talk about your business, and Vistaprint offers business cards at a nominal rate.

Then there are the people in your life. Tell everyone about your business plan. Spread the news on social media. Ask your friends to tell their friends. Look for local businesses that might be willing to work with you. Even your current coworkers can help you put your business out there.

Of course, all the promotional resources in the world won’t necessarily mean that anyone bites. Because you need to give yourself a clear idea of who you’re starting this business for.

For example, are they…?

Teenagers? Young professionals? Seniors?

Figure out who your target demographic is, figure out where you can find them, and put yourself out there.

You’ll stand a better chance of finding the perfect client if you have an idea of who might be interested in the first place.

It’s also a good idea to start working on your dream before you leave your day job so that by the time you leave, you’ll already have a few loyal customers.

This will also help you stay motivated and moving forward with your dream.

Doubt #2: What if I Don’t Make Enough Money?

Creative pursuits tend to be less sturdy than others, but that doesn’t mean that you won’t make as much money as you do in your current job.

Research the current market to get a feel for how much money people in similar careers make, as well as how the most successful people in your dream industry get their success.

Then look at your own situation. Make a plan: what are your expenses, how much can you reasonably charge for your skills, and how much business would you need to do that?

Give yourself a little padding, and set as your production goals when you’re starting out. As your business grows, so can your aspirations.

It’s important to save before you leave your day job. You should have at least 3-6 months worth of expenses in savings when you finally turn in your resignation.

Creative business tends to be feast or famine, but the famines are manageable if you think ahead.

Doubt #3: What if I Don’t Know What I’m Doing?

Remind yourself that no one knows everything right away. There’s information available on the internet and at your local library. You might also be able to learn more from the experiences of your friends and family, on starting a business.

Find it and educate yourself, especially where it pertains to your industry. Get to know creative types who encourage each other, so that you can feel free to ask questions without judgement.

The best way to learn is to admit that you don’t know. You’re not going to be perfect, no matter how much you know. You’re bound to make mistakes, but you can learn from those, too, and your business will ultimately be a lot more successful for it.

Doubt #4: What if I’m Not Good Enough?

This doubt seems specific to creative types. After all, you’re monetizing your creative talents. If your business fails, doesn’t that sort of mean that you’re not good enough to make it work?

Here’s the secret: talent plays a very small role in creativity. Natural talent can give you a boost, but 90% of creative pursuits is a skill acquired through years of practice. It’s like anything else: the more you do it, the better you’ll be.

We like to imagine that creative pursuits work differently from any other skill. We like to imagine creativity as this mystical, whimsical thing that blows in on the winds of inspiration, but that’s not really the case.

Creative work is hard work. It takes commitment and self-forgiveness more than anything. Few people fail because they weren’t good enough.

Most fail because the work turned out to be harder than they expected and they found that they weren’t filled with inspiration every day.

Commit yourself to what you love. Forgive yourself when the work is less than perfect and try again. Allow yourself to grow.

There is a risk in creative pursuits, but there’s risk in any pursuit. Even when you work in a mailroom or a warehouse, there’s risk. You might be injured, your workplace might shut down, or you could get laid off. There’s no way to know what the future will bring.

What you need to remember...

The best way to prevent potential risks is to research thoroughly and make a plan. But don’t allow preparation to become procrastination when it comes to your dreams.

Set a date: give yourself enough time to get ready, but not too much time. Maybe keep a journal to track your progress. And when your doubts creep in, remind yourself that you’re on a deadline and you don’t have time for that kind of negativity in your life.

Your dreams aren't as perfect as they are in your head, but if you shut out your doubts and let yourself try to fulfil them anyway, you may find that they’re better.


Your doubts advice from Josh Elkin


Josh Elkin is the founder of Best Coast Marketing - a marketing agency which helps increase their clients’ traffic through organic link-building. He enjoys writing about entrepreneurship, marketing, productivity and self-improvement.  

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Hi, I’m Rosemary, and I’m a copywriter, editor, and content strategist that specializes in website and blog content for B2C retail and E-Commerce brands. My goal is to help businesses break the communication barriers between consumers and the products they purchase in their everyday lives. So where might you have seen my work? I’ve been featured on popular sites, such as ProBlogger, Search Engine Journal, and Stories by Buffer, and I’ve worked with brands such as E-Bay and Yellowpages. When I’m not working on client projects or studying for my Editing classes, I’m often consuming large amounts of coffee, while enjoying old crime dramas, or listening to indie rock. For more info about my work visit my website,

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